Cinderella Drank My Soul
by Jewannaman
Summary: Pre-Series AU Oneshot where Dan Humphrey and Blair Waldorf are both rich. Includes some Duck (Nothing sexual) as well as Tripp, Carter, and Nate.


_This is a really, really crazy oneshot. Initially, I was going to tag Chuck as well, because he is a significant part of this story, but then I realized that could mislead Chair fans. It's pre-series so some of the characters may seem OOC, but that's only because they're so young. Dan is definitely OOC in this because this is an AU. Also, Tripp is in this, but I have no idea how old he was on the show, so I may be wrong on his age. I believe I'm not off on Carter's age though because he was born on 1989._

* * *

It's happening and there is nothing Dan can do about it. He has less than a minute left, but his eyes are begging not to be opened. When he hears the CD spin in his alarm clock, his eyes open and _Anytime_ from Eve 6 blasts on the speakers. He pulls his T-shirt over his head and takes a shower, trying to desperately lighten the load on his heavy eyes.

Dan was too young to remember the wedding, but he heard it was a memorable one. His father married Lily and a power couple in the Upper East Side was formed.

He grabs a Go-Gurt and rushes out of the penthouse without a goodbye to the lobby where his best friend is waiting for him. As always, Chuck Bass, the son of Bart Bass, is holding a smirk. Dan would hold a smirk too if he was going to be handed Bass Industries.

Chuck spread's his arms wide. "Daniel"

"Thank god it's Friday" Dan says and slaps hands with Chuck

* * *

Like every day at 7:46 A.M. sharp, Blair watches Dan Humphrey climb up the steps and set right below in his camel dye pants. He lifts the messenger bag over his head and she gets to take in his slim-fit dress shirt sticking to his lean body.

"Hi Dan" Serena greets cheerily and waves at him. "Didn't catch you during breakfast"

Dan's eyes never leave Blair's. "Good Morning Blair"

Her lips curve slightly as her eyes remain on him. "Humphrey" Serena might as well be invisible. "I'm actually happy you dropped by. Would it be possible for you to buy me and Serena cup of coffee from Eleven Madison Park?"

"But I don't want coffee" Serena says, ruining everything.

Of course Serena has no idea what game their playing. If her best friend had ever watched _The Princess Bride,_ then she would have a clue of what they were doing.

"As you wish" Dan answers, ignoring Serena's comment.

Her heart clenches and her breath shortens. She thinks he can probably see her chest heave noticeably back and forth. This boy is going to be the death of her.

Every morning, Dan climbs the step and waits for her to make a request. As each day passes, she makes sure to request something more challenging and he has yet to deny her. Not only is Eleven Madison Park out of the way, but it is practically impossible to get inside with the line waiting outside.

She watches him slowly rise to his feet and head down the steps.

"What the hell is up with you two?" Serena asks.

Oh how inane her best friend truly is. How is it not obvious what's going on? He makes her feel things she has never experienced before. Dan Humphrey causes her heart to race and ignites a fire within her that she has never known existed.

"Nothing out of the ordinary" Blair sighs.

* * *

The bell rings and Nate looks to his right to see an empty desk. A crease forms in-between his brows as he had seen Blair sitting on the MET Steps earlier that morning. It's very unlike her to skip class. He looks to his left and sees Blair's best friend. His eyes trail up from her tan legs to her golden sunshine hair.

"Psst" Nate attempts to get Serena's attention. "Do you know where Blair is?"

"No idea" Serena shrugs her shoulders and notices Nate sigh. "Is something wrong?"

Everything is wrong. Blair has been acting strange since school started up again. She doesn't fight for his attention anymore. He had become accustomed to receiving random presents that were her way of seeking attention, but now, he doesn't even receive texts from her. At the time, he found it annoying, however he can't help but miss it now.

"Don't you think something is off about Blair" Nate wonders out loud.

"I think she realized that trying to force you into being a better boyfriend was pushing you away" Serena tells him.

"You think I'm a bad boyfriend?" Nate asks, pointing to himself with his brows furrowed in confusion.

Serena shakes her head and sighs sadly. "Oh Natie"

* * *

Blair skips first period and follows Dan over to the restaurant. As always, Chuck is with him and she can't help but rolls her eyes. That is one combo she will never understand.

"I can't believe I'm doing this" Chuck whines and Blair overhears as she walks right behind them.

"Come on, I'm just taking the advantage of being best friends with the great Chuck Bass" Dan says and nudges shoulders with him playfully.

She can't believe he found a way to pull it off.

"Listen, I get there is something thrilling about corrupting someone untouched, but it's not worth all this trouble" Chuck replies, leading Blair to scrunch her nose in disgust.

Dan shakes his head. "You're twisted man"

"Yes, he is" Blair chimes in, leading them to jump a little and stop to see Blair standing there with her arms folded across her chest. She presses her lips in displeasure towards Chuck. "Chuck, Dan won't be needing your services today, so why don't you make like the germ you are and infect someone else"

"Wait" A smirk slowly spreads across Dan's lips. "Did you skip class to follow me here?"

Blair breathes her nose and her brown orbs trail down to her matching heels. She can feel her cheeks and the tips of her ears burn up.

Dan eyes go wide and he nods Chuck to give them some privacy.

"I'll give you two a minute" Chuck says and walks away, muttering something she can't hear, but assumes it's bitter.

"What are you doing here Blair?" Dan asks.

She tilts her chin up to see him smiling and swallows hard. "I didn't think this was a plausible request, but low and behold, you were going to pull it off"

Dan shoves his hands down his pockets and lifts his heels a little. "What can I say, Chuck's a really good friend"

Blair bites her lower lip and lets his cologne consume her nose. "You could've said no instead of having to go through all the trouble"

"But I don't want to say no" Dan says softly, leading her breath to be taken away.

She stares into his eyes, feeling at a loss of words. It's always difficult to speak to him. He makes her want to hide in her shell.

"What are you really doing here Blair?"

"I told you already" Blair murmurs quietly.

Dan arches a brow. "Does Nate know you skipped class to be here?"

"We aren't doing anything wrong" Blair replies.

"Right" Dan lips curl a little. "I bet Nate hasn't noticed their aren't two girls fighting over him anymore"

Blair narrows her eyes at him. "He's my boyfriend. I don't need to fight with anyone for him"

"Maybe you should send Goldilocks that memo"

She's surprised Serena has yet to strangle him for calling her that.

"You're not being very nice right now" Blair says, and pouts her lips a little.

Dan eyes soften. "I really not that nice"

She takes a step closer and watches him swallow nervously.

"I beg to differ"

Dan stares down at her lips, causing her pulse to quicken.

"Dan!" Chuck shouts, leading Dan to turn his head over to Chuck. "If we're not grabbing any coffee, then we need to get back to school"

Dan's attention falls back on Blair. "I should get going Blair"

She watches Dan step back, take a bow, and head towards Chuck.

* * *

They arrive in the courtyard already late for second period. Not that Chuck cares, but he knows how important grades are to his best friend. Or at least they were not so long ago.

Dan opens the door for them and they enter the halls of St. Jude's, but as they walk through the halls, they see Tripp and Kat leaving the headmasters office.

Kat spots them and a smile becomes of her lips. "Well if it isn't Chuck Bass and his sidekick"

Chuck jaw clenches tightly as he takes in the curvy tanned red-head. She's a senior that he's been trying to fuck for the past few weeks, but unfortunately, she keeps rejecting his advances. He likes it though. It makes the conquest more fun. Otherwise, he could just continue to fuck randoms which has become dull.

"What's his name again?" Kat asks as she approaches them and eyes Dan.

"Dan" Tripp answers.

There is something slimy about Tripp, and he has to admit he likes it. Where's the fun if everyone follows society's rules. But that's not Tripp Vanderbilt. He'll sell his mother's soul as long as he gets what he wants, but he'll make sure it looks nice and pretty when he does it.

"Oh yeah, Rufus's kid" Kat recalls and smiles devilishly.

From the corner of his eyes, Chuck sees Dan's fingers curl a little. As usual, his friend is letting his trust issues get the best of him. People don't realize Rufus's name makes Dan's blood boil. They think anyone would be proud to share blood with a musical god.

"I got to get to class" Dan says, lips pressed tightly.

Tripp looks over to Kat and raises his brows in amusement. "What's the point now?"

"Where else would we go" Chuck asks, sounding intrigued.

"It's Friday. I say we ditch and smoke some trees" Tripp proposes with that future political smile of his. "I have some yellow-dust Haze"

"Can't. I'm meeting someone in the library after school" Dan tells them, with pure coldness resonating from his eyes.

Dan Humphrey is killing him. He knows what exactly Dan needs to do and it makes him sick to his stomach. But because he wants his best friend to be happy, he'll let it go, no matter how disturbing it is.

Chuck looks over to Dan. "What about basketball later?"

"I'll make it" Dan answers and gives him a reassuring nod.

"Carter told you about tonight's party right?" Kat inquires, pointing to Dan with her index finger.

"Why are you so curious?" Chuck smirks as his eyes darken, leaving Kat to glare at Chuck.

"Yeah, I'll be there" Dan says and starts backing away from them.

When Dan spins around, Chuck sticks out an index finger to request a minute as he catches up to Dan. Chuck places his hand on Dan's shoulder to stop him.

"Why didn't tell me you were hanging with Baizen tonight?"

An amused smile forms on Dan's lips. "Chuck, we're hanging out with Baizen tonight"

"Dan, you have to stop talking to that lowlife" Chuck warns.

"Relax" Dan places his hand on Chuck's shoulder and gives him a soothing a smile. "Carter's harmless"

"You don't see it but you've changed. He's obviously been a bad influence on you" Chuck says.

Dan smirks. "Well, you're not the greatest influence either"

"Maybe, but unlike him, I'd take a bullet for you while Carter doesn't give two fucks about you" Chuck replies, hoping he can get through that thick skull of Dan's, but in the end, he knows Dan's too stubborn to listen.

Dan starts backing away and smiles easily. "I'll see you on the courts alright"

Chuck presses his lips in displeasure. "Right"

* * *

Blair leans the back of her head against the bookcase in the library, placing her bottom lip in-between her teeth, and reads the line from the book over again.

"Hi"

Her eyes lift from the book to see Dan leaning on the hand above her shoulder. He is definitely too close for comfort.

"What are you reading?"

Blair's eyes fall on his lips. "Faulkner"

"Faulkner's overrated" Dan smirks.

A smile filled with amusement spreads across her lips. "Oh really?"

"Yup" Dan nods playfully. "In fact, I have something better"

Blair arches a brow. "And what's that?"

Dan reaches the pocket under his jacket and pulls out a small notebook. He hands her over the notebook, and when she opens it, she sees handwritten pages upon pages.

"I'd like you to read them and tell me what you think" Dan says.

Blair looks up to meet his eyes. "I didn't know you were a poet"

"Well now you know" Dan smiles easily.

Blair's eyes drift over to his neck, where she sees a silver chain underneath the collar of his shirt. She slowly reaches for it and tugs out the vintage long silver chained necklace to study it under her fingers. She finds everything about him so interesting.

Her then eyes shut to the feel of him brushing her hair across her forehead.

"I have to go" Dan tells her softly.

She nods and lets his necklace drop, only to press his notebook against her chest as he leaves her.

* * *

Like always, everyone is late showing up to the basketball court, making Nate furious. When he sees Tripp opening the metal fence door with Chuck, he can't help but roll his eyes. Of course they were smoking. He's actually kind of relieved this is Tripp's last year at St. Jude's. He was getting tired of competing with his cousin on everything.

"Where the hell have you two dickwads been?" Nate asks, throwing his hands in the air.

"I was watching Chuck fall on his face" Tripp says.

Nate looks at Chuck and laughs. "Dude, you don't stand a chance with Kat"

"We'll see" Chuck murmurs quietly.

Nate's eyes flicker over to two kids making their way over to the courts, one of which is Carter Baizen. Nate doesn't know much about him, except that he's a sophomore.

"We'll take Bobby" Nate tells Chuck.

"No way, Carter sucks" Chuck protests.

"Come on man, we all know Dan's hard for him anyway" Nate teases.

Chuck breathes hard through his nostrils and shakes his head. "Fuck you"

"Eh, pretty boy!" Tripp yells, leading Carter to look at them. "You're on Bass's team!"

As soon as Chuck leaves to change, Nate grabs Chuck's arms to stop him.

"Hey, did you warn Dan about Blair?"

Chuck pulls his way out of Nate's grasps. "I'm not saying anything to him"

Tripp slings an arm around Nate's shoulder and smirks. "Having trouble keeping your girl?"

"No, but Chuck's having trouble keeping his friend in line" Nate mutters bitterly.

"He's your friend too!" Chuck snaps.

They were friends for sure, but more in the sense of acquaintances who would have a two minute conversation before parting their separate ways. He knew Dan didn't owe him anything, and that's what worries him most.

* * *

Dan wipes the sweat off his forehead with a towel and checks his phone as he sits on the bench of the basketball court to catch his breath.

**B**: _My heart has never felt heavier_

A small smile spreads across Dan's lips.

"That smile spells trouble" Carter says, sitting beside him. "Blair Waldorf is definitely worth it though"

Dan glances over to Carter. "What do you mean?"

"Have you seen her? She's scorching" Carter says.

Dan's eyes drift over to Nate shooting the ball. "I'm waiting for him to punch me"

Carter leans in. "You're not doing anything wrong. Blair's fair game, especially with Serena in the picture"

He falls into deep thought, thinking of how he got here in the first place. Dan has always had eyes for Blair. She's honest, daring, passionate, and absolutely stunning to look at. Her intellectual wit matches his; maybe even surpasses his if he's truly honest with himself.

"Hey" Carter nudges his shoulders to bring him out of his thoughts. "Look what I got for tonight"

Carter unzips his dufflebag and Dan sees a baggie filled with shrooms.

* * *

They're standing in an abandoned warehouse away from the city and Chuck Bass is actually being a pussy. Carter never thought he could ever say that about him.

"Are you insane!" Chuck whispers harshly.

"Hey, keep your voice down" Carter says and then looks over his shoulder to see the table filled with high stakes poker players.

"What if you lose?" Chuck asks.

"Well I guess daddy just bought me a car" Dan smirks, leading Carter to laugh.

"Stop being a panzy Chuck. Dan's a big boy" Carter says. Not to mention he's a gifted at poker. "Listen, nothing beats a good adrenaline rush, so either get out of the way, or grow a pair and buy in"

Chuck shakes his head and storms off like the little bow-tied bitch that he is.

* * *

Dan loses it all, but it was well worth it. His father's going to have a field day. He can already picture the lecture in his head on how money doesn't grow on trees, which is lame and overused.

"Here you go" Carter smirks and hands him his baggie of shrooms. It's been a while since he had tripped. "You want apple sauce"

"No, I'm good" Dan waves him off and takes a bite off the stem.

It taste like shit and he's already reconsidering mixing it with the apple sauce.

"Dan Humphrey"

He watches Kat enter the kitchen in her tight knee high dress, showing off those curves of hers.

"I heard you two idiots got played" Kat says, folding her arms across her chest.

Dan continues to chew on his shrooms, deciding not to respond. Everything in the Upper East Side spreads like wildfire. It's because of this new website called Gossip Girl which has ruined their life. He wonders when their parents will figure out there is a website confirming all their fears.

"Do you want to grab a drink and tell me about it?" Kat asks, looking straight at Dan and giving him a no good smile.

He checks his phone and sees that it's 9:30. His eyes then drift up to see Kat waiting for an answer.

* * *

Blair lifts her head away from the toilet and flushes. She stands on her feet and waters out her mouth before reaching for her toothbrush. Just as she spreads the toothpaste along her brush, her phone rings. It's ten o'clock and Dan Humphrey is calling her.

"Hello"

"Hey"

Blair twirls her hair in-between her finger nervously. "Hi"

"Is it alright if I come over?"

She stares at her reflection and is surprised to see how wide her smile is. "Sure, where are you?"

"Downstairs"

Her eyes widen. "Uh, okay. Just use the elevator and come straight to my bedroom. Oh, and I'm on the 43rd floor"

"Okay, see you soon"

She hangs up and chugs the mouthwash and then spits it out right away because she accidently swallows some of it. Thank god she's still wearing her Nicole Miller Lurex dress.

Blair rushes out the bathroom and opens the front door to her room.

"Mom!" Blair shouts downstairs.

"Yes dear"

"My friend Dan's coming over" Blair tells her.

"Who's Dan?" Eleanor inquires.

"Mom!" Blair whines and rolls her head back in annoyance.

"Okay okay" Eleanor replies.

"Just make sure to let him know where my room is" Blair says.

"Al-"

Blair slams the door in a hurry and runs over to her vanity to spray her Chanel no. 5 perfume on her wrist and spreads it behind her ear. She then looks herself over in the mirror, trying to make sure there isn't anything off. However, she doesn't get much time because the elevator has arrived and she can hear her mother introducing herself along with her father.

The knob to her bedroom door turns and Dan steps into her room. He's holding a lopsided grin, eyes bloodshot.

Blair stands up from her vanity chair and raises her brows. "What are you doing here?"

His eyes start taking in her room. "I should have you design my room"

She narrows her eyes at him for ignoring her question and watches him stride around her room, lightly tapping his hands together. Blair knows what this is. She's been around Chuck to much not to know he's on something.

Dan's eyes light up. "Is that a cabbage patch doll?"

Blair sighs and shuts her eyes in defeat. "Yes"

"Rocking Waldorf" Dan smirks. He then jumps on her bed, eventually lying on his back to stare at the ceiling.

She joins him and lies beside him, taking in the scent of his shampoo and wondering how she came to this stage in the first place.

"What are you doing home?" Dan asks softly, as he turns his head to look at her.

"I didn't have anything better to do" Blair answers and doesn't let her eyes meet his. "These juniors invited Serena to some party up in Columbia"

Dan turns his whole body to face her and brushes a strand of hair away from her eyes, making her heart flutter.

"I wasn't invited, so I told her my mother was having people over and I wouldn't be able to join her" Blair tells him as she plays with the button of his dress shirt. She can't help but think this is very wrong and Nate wouldn't be very happy.

"Your time is going to come Blair" Dan says and gives her a comforting smile.

Blair tilts her chin up to meet his eyes. "It's fine, I got to spend the afternoon reading your poems"

Dan's eyes light up. "You liked them?"

"I loved them"

"One them is actually inspired by your parents" Dan says turning on his back to stare at the ceiling. "You're so lucky to have parents who love each other that much"

She sighs happily. "I am aren't I?"

* * *

It's way past one and Dan knows he's in deep shit. He climbs up the fire escape in the hopes that his mother is asleep. When he reaches his floor, he slips into his room through the open window and tosses his messenger bag on the bed.

A sigh of relief escapes his lips as he shuts his eyes, but that relief doesn't last very long. He hears his door creak open and his heart drops.

"You broke curfew" Allison states.

"Yeah, I'm sorry about that" Dan replies and brushes past her to head for the fridge in the kitchen. He grabs a carton of milk to take a sip.

"What are we going to do about this?" Allison asks.

Dan places his carton of milk back in the fridge and turns around to face his mother. "There's nothing you can do"

"I think it's clear I haven't been stern enough with you" Allison says, grinding her teeth and scowling at Dan.

He can smell the alcohol reeking out of her breath and it makes Dan hate her even more.

"Fuck you mom. I'm not the same little kid you can slap around anymore" Dan replies, shaking his head and walking back to his room.

As he heads to his room, he suddenly feels a throbbing sensation on the back of his head and hears the sound of glass shattering. Everything from there goes black.

* * *

_For now, this is an oneshot which will be a companion piece to another story I may write one day. That companion piece would start off where the pilot of the TV show did. I still may write another oneshot to this story if I get inspired by an idea, but as of now, I don't have one._

_Anyways, happy holidays!_


End file.
